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Method for preparing indene compounds

A kind of technology of ester compound and compound, applied in the field of preparation of organic compound

Active Publication Date: 2011-03-23
SHANGHAI RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018]In the method provided by the above-mentioned documents, the reaction route is multi-step, very long, too time-consuming, and therefore expensive

Method used

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  • Method for preparing indene compounds
  • Method for preparing indene compounds
  • Method for preparing indene compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Synthesis of indene:

[0047] Under nitrogen protection, 500 milliliters of a 1:1 mixed solvent of anhydrous tetrahydrofuran and anhydrous methanol was added to a 1-liter round-bottomed flask, and then 66 grams (0.5 mol) of 2,3-dihydro-1-indanone were added, The reaction mixture was cooled to below 5°C under stirring, and 1.5 mol of sodium borohydride was slowly added in batches. After the addition, the reaction mixture was slowly warmed up to room temperature and stirred overnight, then 2M hydrochloric acid was added under stirring to make it acidic, and the reaction mixture was washed with 200ml ×2 Extract with ethyl acetate, combine the organic phases, desolventize in another 1-liter round-bottomed flask equipped with a reflux azeotropic dehydration device, then add 200 mL of toluene and 0.5 g of p-toluenesulfonic acid, heat up to reflux, and azeotrope Dehydration, when no water evaporates, cool the reaction mixture to below 50°C, add a small amount of triethylamine ...

Embodiment 2

[0051] 85 grams of dipolyphosphoric acid in Example 1 was changed to 45 grams of trifluoromethanesulfonic acid, the reaction temperature was raised to 90°C, and other conditions were unchanged, and 5.8 grams of 2,3-dihydro-1-indanone were obtained after the reaction . It can be used in the synthesis of indenoid compounds in the next step.

Embodiment 3

[0053] Change the dipolyphosphoric acid in Example 1 to polyphosphoric acid, the quality remains unchanged, and the aluminum trichloride is changed to equimolar anhydrous zinc chloride, while the reaction temperature is increased to 90°C, and other conditions remain unchanged, after the reaction Finally, 4.8 g of 2,3-dihydro-1-indanone was obtained. It can be used in the synthesis of indenoid compounds in the next step.

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Abstract

The invention discloses a method for preparing an indene compound, comprising the following steps that: a raw material of a substituted benzoic ether compound is converted into an indenone compound under the condition of cyclodehydration in the presence of a Lewis acid compounded organic acid or inorganic acid. The indenone compound is reduced to a hydroxyindane compound by a reducer; the hydroxyindane compound is converted to the indene compound through dehydration. The method of the invention uses the substituted benzoic ether compound which is common and easy to prepare to synthesize the indene compound, thereby simplifying the synthesis route and saving cost and allowing for mass production.

Description

technical field [0001] The invention relates to a preparation method of an organic compound, in particular to a preparation method of an indenoid compound. Background technique [0002] Indene compounds are important intermediates for the synthesis of fine chemicals such as active pharmaceutical components and liquid crystals, and are also important raw materials for the synthesis of polyolefins, especially the active components of metallocene catalysts for polyα-olefins. [0003] Inden compounds can be used to synthesize chiral ansa-metallocene catalyst components with very important three-dimensional structural properties. The catalyst components are coordinated by indene compounds or their derivatives and transition metal compounds that can catalyze olefin polymerization . [0004] Changes in the coordination properties (such as changes in the substituents on the ligand) can lead to changes in the performance of the metallocene catalyst, resulting in changes in the prope...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C1/20C07C45/61C07C13/465C07C49/67
Inventor 曹育才周慧马静君刘伟
Owner SHANGHAI RES INST OF CHEM IND